Dimethylcarbamoyl Chloride → HCID 178484733, compound

HRID 1905931Notes

Reaction equation

HRID 1905931 reaction equation
[F:1][C:2]([F:34])([O:6][C:7]1[CH:33]=[CH:32][C:10]([CH:11]=[N:12][NH:13][C:14]([NH:16][N:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:21][CH:20]=2)=[NH:15])=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].C(N(C(C)C)CC)(C)C.[CH3:44][N:45]([CH3:49])[C:46](Cl)=[O:47]>C(#N)C>[F:1][C:2]([F:34])([O:6][C:7]1[CH:33]=[CH:32][C:10]([CH:11]=[N:12][NH:13][C:14](=[NH:15])[N:16]([N:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:21][CH:20]=2)[C:46]([N:45]([CH3:49])[CH3:44])=[O:47])=[CH:9][CH:8]=1)[CH:3]([F:4])[F:5]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 178512773HCID 178512773, compound

Product 1

HCID 178484733HCID 178484733, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1,3-bis{[p-(1,1,2,2-tetrafluoroethoxy)benzylidene]amino}guanidine (29.84 g, 0.06 mol), diisopropylethylamine (15.51 g, 0.12 mol) and dimethylcarbamoyl chloride (129.2 g, 0.12 mol) in acetonitrile (200 mL) is stirred at reflux for 22 hours. The reaction mixture is cooled, and the acetonitrile is evaporated under reduced pressure. The residue is dissolved in ethyl acetate (250 mL), and the organic solution is washed with water, saturated NaCl and dried over Na2SO4. The solvent is evaporated under reduced pressure, and the residue is crystallized from benzene-hexanes to give the desired product as a yellow solid, mp 141.5°-143.5° C. in 92.9% yield.

Workup

  1. temperatureat reflux for 22 hours
  2. temperatureThe reaction mixture is cooled
  3. customthe acetonitrile is evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in ethyl acetate (250 mL)
  5. washthe organic solution is washed with water, saturated NaCl
  6. dry with materialdried over Na2SO4
  7. customThe solvent is evaporated under reduced pressure
  8. customthe residue is crystallized from benzene-hexanes

Sources & evidence

ORD record
ord-56080205d6b1433584149585c52b9c9e
Source dataset
uspto-grants-1987_03
Patent number
US04649148

Reaction notes

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